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7 Saf. - 9 Saf.

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28 Saf. - 2 Rab. I

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28 Rab. I - 30 Rab. I

Compare 270 Vacation Homes in Chappaqua with updated reviews, rates, and availability.

"It was a wonderdul and relaxing stay with the family"

"Very comfortable stay with lots of room to spread out. Interesting older house with many unique features. We were happy to learn that they recently installed a new furnace and a dishwasher. Lots of cookware and dishes. We spread out over two dining rooms for mealtime which worked well for us. "

View of the front and outside of house with driveway and garage.

"Dierdre's home was a perfect spot for our family Thanksgiving. Well located, well stocked, and very well cared for!"

"Property owner was great at communicating and the house was perfect!"

"We had a great stay at this fascinating historic house! The house is exactly as described and the hosts were incredibly responsive, even to a last minute request to extend our stay."

Garrison Vacation Rental | 2BR | 2.5BA | 1,700 Sq Ft | 1 Step to Enter

"Would stay here again "

Highland Falls Vacation Rental | 3BR | 2BA | 1,100 Sq Ft | 2 Stories

"Very well appointed home a short walk from the West Point gate that met all of our needs for a weekend of catching up, going for walks and attending a wedding. Property is close to Storm King Art Center which is a great way to spend a beautiful afternoon. We lost power for 17 hours (neighborhood transformer blew) and the owners could not have been more helpful. Would highly recommend this house. "

"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...

"Host was very accommodating and easy to communicate with!"

SAR 1,984 total

includes taxes & fees

26 Feb - 27 Feb

SAR 705 total

includes taxes & fees

5 Feb - 6 Feb

"Its was perfect, quiet and spacious great little get away."

"Host is kind and welcoming. The place is in a very quiet neighborhood. Plenty of street parking. 25 min from nyc. Highly recommend "

"This was a late holiday gathering of family members from St. Louis and Rye New York. Great and easy spot to get to. Pretty setting with the water view. I am sure in warmer seasons it be great spot for all the outside amenities. Six adults and one baby. Space nice set up. "

SAR 5,698 total

includes taxes & fees

14 Feb - 15 Feb

"We were 9 adult women. There was plenty of space for us to gather as a group as well as sleep. The house is clean and in a great neighborhood. Very easy on and off to the highway to get to our conference in Darien. Highly recommend."

SAR 2,921 total

includes taxes & fees

3 Feb - 4 Feb

White Plains Vacation Rental | 5BR | 2.5BA | Stairs Required | 3,212 Sq Ft

"Beautiful modern home with great views over the pond and woods. Super comfortable and many amenities. I really appreciated how well stocked the kitchen was with pots and pans that you can actually cook with compared to most VRBO's. Only drawback is that the area isn't really walkable. Busy road with minimal shoulder and you can't get down to the pond. We drove to a number of great hikes in the area though. Bonus: the woods behind the house were home to a couple great horned owls calling to...

SAR 3,033 total

includes taxes & fees

3 Feb - 4 Feb

"We had a wonderful stay at the Contemporary Cozy Cottage! Very modern amenities and appliances, and the kitchen had everything we needed!! Nadia always responded promptly, and answered all of my questions. The Cottage is located close to just about everything in the Peekskill, Cortlandt Manor, and Yorktown Heights area. And I would definitely recommend a short drive to the charming little town of Cold Spring which is not too far away. Thank you Nadia!"

SAR 1,403 total

includes taxes & fees

2 Feb - 3 Feb

"This home was perfect for us and our group of friends whom were flying in to surprise a local Bronx friend for his 40th. The bedrooms were great and overall clean and decorated nicely. The location of this home was close to everything from walking distance to a 15-20min drive. We enjoyed the front porch and backyard for a cocktail or two. Not to mention that the house manager was great on communication. Thank you and we highly recommend!"